(S)-(+)-Ibuprofen-d3
カタログ番号 B1507591
分子量: 209.3 g/mol
InChIキー: HEFNNWSXXWATRW-PCXQMPHHSA-N
注意: 研究専用です。人間または獣医用ではありません。
Patent
US04223132
Procedure details
To a solution of benzyl 2-p-isobutylphenylpropionate (3 g) in methylene chloride (18 ml) are added a solution of aluminum chloride (4 g) in nitromethane (50 ml) and anisole (3 ml) at 0° C., and the mixture is stirred at room temperature for 6 hours. The reaction mixture is diluted with ethyl acetate, washed with hydrochloric acid and water, dried and evaporated. The residue is recrystallized with n-hexane to give 2-p-isobutylphenylpropionic acid (186 mg) melting at 75°-77.5° C. Yield 91%.
Name
benzyl 2-p-isobutylphenylpropionate
Quantity
3 g
Type
reactant
Reaction Step One
Yield
91%
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:22])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[N+](C)([O-])=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:22])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3] |f:1.2.3.4|
|
Inputs
Step One
|
Name
|
benzyl 2-p-isobutylphenylpropionate
|
|
Quantity
|
3 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)OCC1=CC=CC=C1)C
|
|
Name
|
|
|
Quantity
|
4 g
|
|
Type
|
reactant
|
|
Smiles
|
[Cl-].[Al+3].[Cl-].[Cl-]
|
|
Name
|
|
|
Quantity
|
18 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
|
Name
|
|
|
Quantity
|
50 mL
|
|
Type
|
solvent
|
|
Smiles
|
[N+](=O)([O-])C
|
|
Name
|
|
|
Quantity
|
3 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)OC
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the mixture is stirred at room temperature for 6 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
washed with hydrochloric acid and water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
evaporated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The residue is recrystallized with n-hexane
|
Outcomes
Product
Details
Reaction Time |
6 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 186 mg | |
| YIELD: PERCENTYIELD | 91% | |
| YIELD: CALCULATEDPERCENTYIELD | 8.9% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US04223132
Procedure details
To a solution of benzyl 2-p-isobutylphenylpropionate (3 g) in methylene chloride (18 ml) are added a solution of aluminum chloride (4 g) in nitromethane (50 ml) and anisole (3 ml) at 0° C., and the mixture is stirred at room temperature for 6 hours. The reaction mixture is diluted with ethyl acetate, washed with hydrochloric acid and water, dried and evaporated. The residue is recrystallized with n-hexane to give 2-p-isobutylphenylpropionic acid (186 mg) melting at 75°-77.5° C. Yield 91%.
Name
benzyl 2-p-isobutylphenylpropionate
Quantity
3 g
Type
reactant
Reaction Step One
Yield
91%
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:22])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[N+](C)([O-])=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:22])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3] |f:1.2.3.4|
|
Inputs
Step One
|
Name
|
benzyl 2-p-isobutylphenylpropionate
|
|
Quantity
|
3 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)OCC1=CC=CC=C1)C
|
|
Name
|
|
|
Quantity
|
4 g
|
|
Type
|
reactant
|
|
Smiles
|
[Cl-].[Al+3].[Cl-].[Cl-]
|
|
Name
|
|
|
Quantity
|
18 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
|
Name
|
|
|
Quantity
|
50 mL
|
|
Type
|
solvent
|
|
Smiles
|
[N+](=O)([O-])C
|
|
Name
|
|
|
Quantity
|
3 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)OC
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the mixture is stirred at room temperature for 6 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
washed with hydrochloric acid and water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
evaporated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The residue is recrystallized with n-hexane
|
Outcomes
Product
Details
Reaction Time |
6 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 186 mg | |
| YIELD: PERCENTYIELD | 91% | |
| YIELD: CALCULATEDPERCENTYIELD | 8.9% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US04223132
Procedure details
To a solution of benzyl 2-p-isobutylphenylpropionate (3 g) in methylene chloride (18 ml) are added a solution of aluminum chloride (4 g) in nitromethane (50 ml) and anisole (3 ml) at 0° C., and the mixture is stirred at room temperature for 6 hours. The reaction mixture is diluted with ethyl acetate, washed with hydrochloric acid and water, dried and evaporated. The residue is recrystallized with n-hexane to give 2-p-isobutylphenylpropionic acid (186 mg) melting at 75°-77.5° C. Yield 91%.
Name
benzyl 2-p-isobutylphenylpropionate
Quantity
3 g
Type
reactant
Reaction Step One
Yield
91%
Identifiers
|
REACTION_CXSMILES
|
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:22])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[N+](C)([O-])=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:22])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3] |f:1.2.3.4|
|
Inputs
Step One
|
Name
|
benzyl 2-p-isobutylphenylpropionate
|
|
Quantity
|
3 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)OCC1=CC=CC=C1)C
|
|
Name
|
|
|
Quantity
|
4 g
|
|
Type
|
reactant
|
|
Smiles
|
[Cl-].[Al+3].[Cl-].[Cl-]
|
|
Name
|
|
|
Quantity
|
18 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
|
Name
|
|
|
Quantity
|
50 mL
|
|
Type
|
solvent
|
|
Smiles
|
[N+](=O)([O-])C
|
|
Name
|
|
|
Quantity
|
3 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)OC
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the mixture is stirred at room temperature for 6 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
washed with hydrochloric acid and water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
evaporated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The residue is recrystallized with n-hexane
|
Outcomes
Product
Details
Reaction Time |
6 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 186 mg | |
| YIELD: PERCENTYIELD | 91% | |
| YIELD: CALCULATEDPERCENTYIELD | 8.9% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
